Which AE shoe to buy??

I am just starting to purchase quality shoes and today purchased the AE Strand in Walnut and the AE Park Avenue in Black after advice from the forum.

Here is my question/dilemma? After reading more threads and articles than I can count, I still can't tell if AE Walnut Strands go with denim in a business casual/casual setting. I am going to purchase a pair of AE's and can't decide on what to go with?

#1 Can the AE Walnut Strand's I bought today work with denim? I am guessing they will work but not the greatest?

#2 What should be my next purchase for with jeans? A monkstrap? A chukka? If one of these what model recommended. Thank you in advance for the help guys.

How does the AE Chelsea compare to other brands? Trying to keep cost around $300 or less. The AE description says it has a rubber sole. Here is description.

Allen Edmonds Ashbury Description:
Exclusively from Allen Edmond's Boot Collection, Ashbury is modeled after a Chelsea style boot, popular in the 1960s. This high quality boot is constructed from a traditional welted process. Made with close attention to detail, you can be sure this durable boot will stay in style. Casual, sophisticated. Ashbury.